Cesium carbonate → HCID 67043864, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave vial was placed 6′-bromo-3,4-dimethoxyspiro[cyclopentane-1,2′-inden]-1′(3′H)-one 1st isomer (51 mg, 0.157 mmol), 3-cyanobenzeneboronic acid (30 mg, 0.204 mmol), PdCl2(PPh3)2 (11 mg, 0.016 mmol) and cesium carbonate (128 mg, 0.393 mmol). This solid mixture was dissolved in a Dioxane/water mixture (2.0 mL, 6:1 ratio, respectively). The solution was purged with a N2 stream for 30 seconds. The vessel was placed in the μwave and heated to 110° C. for 30 minutes. After that time, the mixture was filtered through a Celite plug. The plug was rinsed with dichloromethane (4 mL) and water (4 mL). The phases in the filtrate were separated. The aqueous phase was back-extracted with dichloromethane (2 mL). The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated under reduce pressure. The crude material was purified by flash chromatography (ISCO, 12 g SiO2 cartridge, ethyl acetate/hexanes as the eluents). The corresponding fractions were combined and concentrated under reduce pressure yielding 3-(3,4-dimethoxy-1′-oxo-1′,3′-dihydrospiro[cyclopentane-1,2′-indene]-6′-yl)benzonitrile 1st isomer (40 mg, 0.115 mmol, 73% yield).

Provenance & Evidence